SD: Mark, you’re not like other CFOs. You have gone in and out of being CFO so many times, and because you’ve been on multiple sides of the board table, I felt it would be interesting to hear your perspective. So to start off – which job do you prefer – the CFO Job or the outside advisor job?

MM: It’s not as simple as that. I live to do two things – One is to advise founders and management teams, and the other is to do complex financial transactions. The thing that I liked about being a CFO at start-ups is that they were often in need of both. When I created SurePath Capital Partners, I created a company that only does both those things. When I had been a CFO and had been a close advisor to the CEO’s that I’d served and got to work on lots of transactions, then I’m a really happy guy. If I’m the CFO of a company and it’s well capitalized and were not doing acquisitions, and we’re not being acquired – if we’re just kind of running the ship, then that’s not so great for me.

Quick Takes from Mark on…Thinking out of the CFO boxYou need to go way beyond finance. You need to step up and fill other operating capacities.Relationship between CEO and CFOSynergy – if the CEO is the technical founder, take on the more outward-facing aspects; if the CEO is outward-facing and a rainmaker, try to take on as much of the internal operations as possible.

Create an informal network of your peers

There are always folks who are a little bit ahead of you in terms of scale and experience and complexity, and you can learn a ton from them. Branch out to other Venture funded CFOs.

Capable management

The whole thing about being a C-level executive in a venture backed company is that your competency and leadership need to scale faster than the company is scaling.

Keeping sight of the bigger picture

Remember to not only work IN the business, but to also work ON it. Similarly, to not just work IN yourself, but also to work ON yourself. Delegate lesser tasks to free up time to work on growing your capacity.

SD: Let’s talk about what it takes for a technology CFO to be successful. You’ve played that role, you’ve advised people in that role, what makes a successful Tech CFO?

MM: Well, I’d say it is the ability to go way beyond finance. I think, when a company isn’t fund raising, the financing role is pretty simple, and you have to find other ways to add value. Often the management teams at start-ups are incomplete and so there’s room to go way beyond finance and fill in other operating capacities. I’ve definitely done that a lot. I’d say within the finance realm, first of all you have to have a very clear understanding of all the nuts and bolts in the business, particularly because often those businesses are burning money and so you must understand ‘good burn’ vs ‘bad burn’. Most businesses these days hinges on profitable unit economics, and so even though the business as a whole might be in the red, if these customers are profitable, and you understand the nuances of customer mass, that’s kind of crucial. And then I would say the ability to translate. For example, if you’d just walk in to an exec meeting and rattle off a bunch of numbers and metrics, it’s sort of somewhat useful, but you have to go way deeper. As an example, if “churn” (the number of people who cancel your service) has moved in one direction, its somewhat useful to give the data points on the movement, but it is far more useful to understand the root cause and give good guidance. So again, it’s being able to go beyond the numbers.

The approach I’ve always taken to the CFO world is to define the role in a way that gives the CEO maximum leverage. What I mean by that is – if the CEO is very technical founder, then I’ve always tried to take on some of the outward facing aspects, so that the CEO would be able to be building and shipping product. Whereas if that CEO is a very outward facing CEO and a rainmaker, then I’ve tried to take on as much as the internal operations as possible, so that person could be out of the office and know that things are still running. To me the CFO is the right hand of the CEO, and therefore you have to govern yourself or kind of define the role in a way that has the most impact on the CEO.

SD: You’ve been a CFO on a full time basis and CFO on part time basis. What’s the difference?

MM: Huge difference. Again, take everything I’ve said about taking on more operating responsibility, in the context of full time. If you think about the core of a business – the core of any business in the technology business is building product and selling product, just to generalize. The rest is in support of that. In that context, finance is always important, but it’s not a core thing. It’s relatively horizontal. It can transfer the same functions from one company to the next. And so outsourcing the core nuts and bolts of finance makes all kind of sense. But where you run into trouble is when you outsource finance to someone, but then try to get that someone to do a whole bunch of other things – that just doesn’t work. So the big difference for me is that when I was full time I was going way beyond the finance role, whereas when I was part time I stuck to the core nuts and bolts of running a very tight back office, investor relations, budgeting, fundraising, reporting, etc.

SD: I’ve asked number of tech companies who are looking for finance help “what do you need?” and they said “well, we would like a Mark MacLeod”. You have a brand to you that says “start-up tech CFO”. How would you recommend they find their own Mark MacLeod?

MM: That’s a tough one. You know it’s funny. In retrospect, it might have taken the hard way to get my experience. My first start up was a client of mine and I came in with absolutely no experience and just kind of stumbled along. And because I was very focused on deals and fund raising in particular; if I didn’t feel like that company was on the trajectory to really grow massively, I’d move on. And that resulted in a bunch of things. I exited positively in a relatively short time frame, or me concluding that they weren’t going to be exiting in a relatively short time frame. But the point of all that is my learning and development was compressed and accelerated by moving to different companies and getting exposure to different start-ups, different stages in their life cycle, and that whole bit. So that’s one path.

I was very lucky because I got into start-ups very early, back in the late 90’s when anyone with a pulse was getting funded. The environment was pretty forgiving. So that could be a path today – someone who has kind of hustled around and has been involved in some fund raising, and has shown a propensity and an aptitude to be able to talk about things that are beyond the numbers.

But I’ll tell you… the whole thing about start-ups and venture capitalists is it’s all about the outliers. And while I’ve been part of some great businesses, the biggest learning opportunities and the biggest development, the most scope and the most exposure is when I was part of the outliers. Like Shopify and Freshbooks. So the point of that is hiring someone with that pedigree, even if they haven’t had the CFO title. If you’ve gone through Shopify’s growth, from 100 to 700 people, if you’ve gone through all the things that come with that and you understand how systems scale and you understand how to do really amazing investor reporting, and how to build sophisticated budgets and how to scale a finance function, that’s amazing experience. I’ve learned through trial and error that QuickBooks falls apart when you cross 100 employees. And then you end up having to go to a NetSuite or an Intact or something. Knowing that coming in, because you’ve come from a place with scale, would be pretty interesting.

So it’s really 2 different profiles. It is someone who is really helpful and has had some exposure through a few different companies so that they can pattern match. Or it’s someone who has come from a bigger company, one that the start-up aspires to be.

SD: Am I correct in saying that nobody can really hire Mark MacLeod because Mark learned it from the companies that he did the work in? I mean, you’re beyond that start-up age CFO that is young and has just enough experience but not too much, who’s not looking to take home too much cash and is more willing to put it down for the future. Do I understand that correctly?

MM: If someone wants to hire a Mark MacLeod, well a Mark MacLeod has been 2 decades in the making and is still being made, you know what I mean? They don’t exist. You have to hire someone who looks nothing like what I look like now. Hire someone who I was like 15-20 years ago, which means you’re really taking a chance. I got in because the environment was so frothy. And I would say that I stayed for 2 reasons – 1 maybe as you said, I don’t look like most CFO’s, because it’s never been just about the numbers for me, it’s always been about the strategic context around the numbers. So it was always the bigger picture. I’d say the thing that really helped make me stand out is I had a huge passion for venture capital. And for getting into the venture community and making deals happen. If a company is running out of money and hiring you helps them get money, then that should really sell itself. But in the early days that’s really how I got into a lot of start-ups. When I was doing the part time CFO stuff, the real sweet spot was that I would take companies and get them ready for the next round of funding, I would raise it for them, and then stay on as their CFO. That’s how I was kind of paying my way. So it’s a different context.

SD: What’s the ideal CFO for you to work with?

MM: I don’t know that there is just one to be honest. If I am helping a company fundraise or helping them prepare for an exit, I think that in both cases the deal will very much be driven by the strength of the management team. It’s not like I simply want a technician in there because I can handle the strategy stuff. I’d be more than happy to work with a very strategic deal-making CFO. I think that doing great big deals is a team sport, not like an individual hero sport. I think I’m equally happy to work with an internal deal maker, as I am to work with someone who’s got super tight back office. I think the takeaway is that one way or the other, we need both. So if the person is just the big deal maker and the back office is not super tight, that’s going to make it harder for me to do what I do. One way or another we have to have both the substance and the spot.

SD: What advice would you give to new CFOs who are just at the start of their career?

MM: Talk to peers a lot. There’s always folks who are a little bit ahead of you in terms of scale and experience and complexity, and you can learn a ton from them. You could also create an informal network, talking to other venture funded CFOs and the portfolio. Makes a ton of sense. I think this is true not just for CFOs but for any role. The whole thing about being a C-level executive in a venture backed company is that your competency and leadership has to scale faster than the company is scaling. And so in that context, having a coach who can help you work through issues and help you scale is super important as well.

SD: How did you make time for important things? Things that were related to your career and employer, but there was no deadline attached to it?

MM: I think I have a certain level of self-awareness. So I knew that I needed to not only work IN the business but also work ON it. And similarly to not just work IN myself, but to also work ON myself. I never have been the kind of technician who is always dotting I’s and crossing T’s. As a result I was able to push that kind of work down to the right level and that gave me capacity to work on growing my capacity, if that makes sense.

+++++++++++++++++++++

Samuel Dergel is a Principal with Dergel Executive Search. He is an executive search consultant, executive coach, blogger, speaker, trainer and author.